Characterizing the epoxidation process conditions of canola oil for reactor scale-up

Monono, Ewumbua; Haagenson, Darrin M.; Wiesenborn, Dennis P.

doi:10.1016/j.indcrop.2015.01.061

Cited by 28 publications

(26 citation statements)

References 22 publications

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“…Even with lower amounts of reagents, the conversion at 2.5 h for this 3 kg batch was 3% higher than the 75% conversion observed in a previous study. 14 The viscosity values in Table 5 show a strong relationship with conversion value (r = 0.97) as was also observed among values in Table 2.…”

Section: Organic Process Research and Developmentsupporting

confidence: 70%

“…12,13 Varying the H 2 O 2 addition rate influences the conversion rate; however, this effect is minimal if all the required amount of H 2 O 2 is added at least 1.5 h before the end of the reaction. 14 The five main factors that directly influence oxirane formation are molar ratio of H 2 O 2 to unsaturation, molar ratio of acetic acid to unsaturation, amount of Amberlite catalyst, reaction temperature, and reaction time.…”

Section: Sefose Derivedmentioning

confidence: 99%

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Optimizing Process Parameters of Epoxidized Sucrose Soyate Synthesis for Industrial Scale Production

Monono

Bahr

Pryor

et al. 2015

Org. Process Res. Dev.

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There is a growing need to produce epoxidized sucrose soyate (ESS) at an industrial scale for large-scale applications in coatings and material science. Industrial scale production of ESS requires optimization of the process conditions to minimize cost without compromising resin quality. Therefore, a robust model was developed that predicts the conversion of double bonds to oxirane under different process scenarios. Data for the model were obtained by epoxidizing 30 g batches of sucrose soyate at three reactor temperatures (55, 60, and 65°C), three molar ratios of acetic acid to oil unsaturation (0.25:1, 0.375:1, and 0.5:1), three molar ratios of H 2 O 2 to oil unsaturation (1:1, 1.5:1, and 2:1), three catalyst amounts (1.5, 3.75, and 6 g), and three reaction times (3.5, 4.5, and 5.5 h). The model was highly significant with an adjusted R 2 of 97.6% and predicted R 2 of 96.8%. The root-mean-square errors (RMSE) of 0.54 showed that the model was a good fit in predicting optimal epoxidation conditions at different process levels. ESS samples epoxidized at 60−65°C for 4.5−5 h had conversion greater than 98% even when reagent amounts were reduced by 18−20%. A similar resin quality was also attained when one of the optimal conditions was scaled-up 100 fold to a 3 kg batch. Therefore, this model can be used to determine appropriate processing conditions for epoxidizing vegetable oil-based compounds at any scale with sufficient mixing and temperature control.

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Section: Organic Process Research and Developmentsupporting

confidence: 70%

Section: Sefose Derivedmentioning

confidence: 99%

Optimizing Process Parameters of Epoxidized Sucrose Soyate Synthesis for Industrial Scale Production

Monono

Bahr

Pryor

et al. 2015

Org. Process Res. Dev.

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“…The differences in double bond conversion clearly narrowed as the reaction reached 4 h and beyond even though differences were observed in the average reaction temperature (1-2 • C) and the H 2 O 2 addition rate for these batches. In our previous 300 g batch experiment in which reaction temperature was not controlled within the optimum range, the conversion was at least 83% complete at 2.5 h and up to 99% by the end of 5.5 h (Monono et al, 2014). In this study, there was a steady increase to 99% of double bonds converted to oxirane groups up to the 5.5 h reaction time.…”

Section: Evaluating the Performance Of The Reactorsupporting

confidence: 45%

Pilot scale (10kg) production and characterization of epoxidized sucrose soyate

Monono

Wiesenborn

2015

Industrial Crops and Products

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“…In general, the epoxidation of vegetable oils using the Prilezhaev method requires several hours to obtain high conversions . To enhance the perhydrolysis rate, various catalysts can be used, such as enzymes, metals, metal oxides, sulfuric acid and acidic ion exchange resins (AIERs) . A summary of several epoxidation processes in the presence of various homogeneous and heterogeneous catalysts is presented in Table .…”

Section: Introductionmentioning

confidence: 99%

“…The exchange reactions take place in an aqueous environment retained by the ion exchanger, which is generally termed gel water or water swelling . Epoxidation with AIER has been conducted for a wide variety of oils and operation conditions, and it is the most reported method because catalyst separation is easy and side reactions are suppressed . Ion exchange resins are the most active, selective and inexpensive catalysts available for this process.…”

Section: Introductionmentioning

confidence: 99%

Screening of ion exchange resin catalysts for epoxidation of oleic acid under the influence of conventional and microwave heating

Aguilera

Tolvanen

Eränen

et al. 2019

J of Chemical Tech & Biotech

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BACKGROUND For many chemical systems, it is of great importance to find a durable, active and efficient catalyst that improves the process performance. Epoxidation of oleic acid with peracetic acid (Prilezhaev oxidation) was carried out in an isothermal loop reactor in the presence of heterogeneous catalysts. The kinetic experiments conducted under microwave heating (MW) were compared with identical experiments carried out under conventional (conductive/convective) heating. Extensive screening of heterogeneous catalysts was conducted and the influence of microwave irradiation on the reaction kinetics was studied. Several ion exchange resins were screened to explore their applicability and activity in the epoxidation of oleic acid. The perhydrolysis reaction (peracetic acid formed in situ from acetic acid and H2O2) was promoted with the use of various solid acid catalysts: Amberlite IR‐120, Amberlyst 15, Smopex®, Dowex 50x8‐100, Dowex 50x8‐50, Dowex 50x2‐100 and Nafion™. RESULTS From the selected group of catalysts, Dowex 50‐x8100 and Dowex 50x8‐50 produced the highest yield of epoxidized oil. Only minor differences in the reactant conversion and the product yield were found in the experiments carried out under microwave exposure compared to the conventionally heated experiments in the presence of several ion exchange resins. CONCLUSIONS The catalytic effect was much more prominent than the microwave effect, because the solid acid catalysts enhanced the slow step of the process, the perhydrolysis of acetic acid. The catalytic effect was very dominant and a considerable improvement of the oleic acid conversion and the epoxide yield was observed in the presence of the top‐performing catalysts. © 2019 Society of Chemical Industry

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Characterizing the epoxidation process conditions of canola oil for reactor scale-up

Cited by 28 publications

References 22 publications

Optimizing Process Parameters of Epoxidized Sucrose Soyate Synthesis for Industrial Scale Production

Optimizing Process Parameters of Epoxidized Sucrose Soyate Synthesis for Industrial Scale Production

Pilot scale (10kg) production and characterization of epoxidized sucrose soyate

Screening of ion exchange resin catalysts for epoxidation of oleic acid under the influence of conventional and microwave heating

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